AI Will Revolutionise How You Travel, Priceline CEO Says
4 min
With its 1997 launch as a name-your-own-price site, Priceline helped usher in the era of online travel booking―and the growth of a trillion-dollar category. Priceline itself has mushroomed into a global business with 1,500 full-time employees; along with global airline bookings, the site claims to offer 1.2 million accommodations in 116 countries.
Now, the Connecticut-based company is focusing on generative AI, and CEO Brett Keller is behind the leap. It’s just the latest technology push from Keller, a 25-year veteran of the company who has also served as CMO and COO. Under Keller, Priceline launched the travel industry’s first full-service mobile app in 2009; he also helped conceive the hugely popular William Shatner-fronted “Negotiator” ad campaign.
Keller, 56, talked to Penta about how AI is changing travel planning, what luxury travellers do to save money, and why Japan blows his mind.
Penta: Much of Priceline’s marketing is about value. Do you see luxury travellers in your customer mix along with budget-conscious travellers?
Brett Keller: High-net-worth consumers take a significantly higher number of trips than the average leisure traveller. For a high-end vacation like a safari in Tanzania, they’ll work with experts. But for the other 30 trips they book that year, either for themselves or family members, they don’t always reach for the stars. They want to manage money effectively. And as they’re moving around the country and the world, they need a fast, easy way to book travel that accommodates their needs. Priceline is a great platform for that kind of trip. And if you’re taking a quick weekend trip to Miami, and want to stay in the Four Seasons, we’ve negotiated with them. Even high-net-worth individuals seek value.
Priceline made headlines last year for partnering with both Google and OpenAI on Penny, your AI assistant. How has Penny evolved?
She’s gone from, “I can answer questions about the hotel you’re looking at” to actually servicing the customer through more complicated scenarios. If you need to cancel a hotel that’s fully refundable, you can do it with one click. But if there are issues, like a reservation that’s not fully cancelable, Penny can walk through those steps for you.
Penny’s also helping people find, search, and book properties. For example, if the customer tells her, “I’m looking for a great resort with these features, anywhere warm”—she’ll present recommended properties that meet those requirements. You can continue with Penny on the site, or go with the traditional experience.
Has there been any pushback from consumers about Penny and generative AI?
There has been none. Customers still have access to phone agents. Anyway, the younger generation doesn’t want to talk to anyone. And with traditional chat agents, live agents, or even messaging apps, there’s typically a delay. Penny answers immediately and in real time.
What’s the future of generative AI and online travel booking?
The future is a highly personalised shopping experience. It’s hard to achieve, because we don’t know about the consumer when they come in. But generative AI lets us dramatically improve personalisation. As you work with Penny, and tell us your preferences, the way you interact lets us find and book the best products and services every time you return. The ability to customise and personalise increases exponentially.
Is the travel experience even more bifurcated between elite, ultra-high-net-worth travellers and everyone else?
Consumers seem to be a little less sensitive in some areas. On planes, first-class and comfort-plus seats are the first to go, most of the time, and people are burning through points to sit in the front because they’re tired of not having legroom. But seats are packed in economy, too, so people are flying.
Hotel bookings are more economically driven in the U.S. Higher-income people are not as affected by interest rates or the cost of living, so they spend more freely than economy-minded consumers. There is a bit of bifurcation there. The low end is not filling, but the high end is.
It’s been reported Europe’s going to get even more crowded this summer. Does Priceline ever suggest alternatives to over-touristed or overpriced destinations?
We’re not in the business of telling you where you shouldn’t travel. We market popular destinations because that’s where people want to go. As much as we could tell people, “Las Vegas is overcrowded, don’t go,” people will want to go.
Social media is highlighting some overpopulated destinations and suggesting alternatives, so that comes back to us. But price is the No. 1 motivator. Vegas is a great value. There are so many hotel rooms available that you can go in a non-peak period and get a room in a four-star hotel for US$120. Try doing that in New York City.
What destinations are going to pop over the next year or two?
Asia will continue to be exciting and interesting to people. Bangkok is a great place to move in, then travel throughout Southeast Asia. As the region gets more popular, people will keep trying to find more remote and more unique destinations. People love Europe, but it was the hot spot in 2022 and ’23. Some travellers are saying, “I’ve had enough, and I’m moving on.” Japan is also amazing, for so many reasons. It’s easy to navigate. English is not a challenge. It’s safe. It feels like a different world, but completely first-world. The strength of the dollar is also driving some of that―again, price plays a role.
Beyond that, Mexico and the Caribbean took a real hit in 2022 and ’23 after a boom in 2021. They’re coming back now. A lot of people don’t want to travel far—“I just want to go to a beach and not think of anything.” And because not everyone wants to travel overseas, unique and relaxing cities like Nashville, Tennessee; Houston; and Austin, Texas, will be popular, especially into the fall.
Every day brings more headlines about airline woes. Who gets blamed if a Priceline customer has a bad flying experience, you or the airline?
When you have a bad experience traveling, you want to blame everybody. No matter what happened, the online travel agency takes blame and the airline takes the blame. It could be your seat, the person sitting next to you, whatever. We get the complaint, and we take on that responsibility and that role. We have leverage because of the amount of business we drive to partners. They want to work with us to make sure the customer has the best experience. Something goes wrong almost every time you take a trip. That’s just the reality.
What are your favourite places to travel?
My favourite destination, and a place where I spend a lot of time every summer, is [resort town] McCall, Idaho, one of the most beautiful towns in the West, with hiking, trails, and mountain biking. Outside of the country, it’s Japan, absolutely. Tokyo is the most exciting city in the world. It’s mind-blowing.
This interview has been edited for length and clarity.
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The ultimate trading-floor flex? A Snoopy Swatch. Or a Casio calculator. Why lots of money men (still) favour novelty watches.
3 min
How do you tell the time? Neal W. McDonough, the COO of a finance and policy startup in Ho-Ho-Kus, N.J., looks to Charlie Brown, the loveable, miserable “Peanuts” protagonist. An illustration of the character occupies the exec’s watch dial, Brown’s stout arms acting as the minute and hour hands.
McDonough, 55, bought the kooky Timex for a Valentine’s Day trip about five years ago, along with a matching model depicting Lucy van Pelt (Brown’s frenemy) for his then-girlfriend. To his surprise, he kept wearing the $150-ish ticker after the trip. “It’s now my business watch,” he said, adding that such a non luxury model can telegraph that he’s under no obligation to be flashy. “I have nothing to prove to anyone,” he said. “And the fun thing is, a lot of people notice [my watch].”
Though finance guys famously flaunt Rolexes or Patek Philippes on their wrists, an established subspecies of money men goes the other way entirely. In place of a sleek steel case and elegant ceramic dial? Mickey Mouse. SpongeBob SquarePants. Fanta-orange rubber straps.
Over the years, highfliers have made headlines for sporting Swatches. (See: Blackstone Group CEO Stephen A. Schwarzman or former Goldman Sachs CEO Lloyd Blankfein .) That “wealthy guy, cheap watch” ethos continues to resonate in boardrooms and on trading floors, with men of all seniority levels embracing plasticky, offbeat designs, from superhero models to calculator Casios. Many resemble something you might win in a claw machine. Priced from $30 to a few hundred bucks, they’re a bit of fun and a different sort of flex, conveying an “I don’t need a Rolex” bravado that comes from having made it. Call them anti-status watches.
Patrick Lyons, the managing partner of a family office in New York, rotates two contrasting watches: a 1988 Santos de Cartier and a Nickelodeon “SpongeBob SquarePants” model with a tangerine strap.
The Cartier, a family heirloom, is a slice of French sophistication; the Nickelodeon dial features a giant image of a pink starfish named Patrick Star who lives under a rock. Lyons, 35, likes that the second watch is idiosyncratic—and that its starfish shares his name. “I wear that more often than my Cartier,” he said, adding that he hopes to pass down both models to future offspring.
Leroy Dikito, 42, an executive director at JPMorgan Chase in New York, chose his $450 “Avengers” watch from Citizen because it reminds him of his father, who loved comic books. Though its stainless-steel strap reads urbane enough, its cheerfully garish dial slices together images of the Hulk, Iron Man, Captain America and other superheroes. Working in finance, you need to be “serious all the time,” so a fun watch brings welcome levity, said Dikito. “People need to know there is more than the big job and the title.”
Since a suit can only inject so much color, a watch offers that rare opportunity to “show off your personality,” said Eli Tenenbaum, 36, the director of corporate development for a New York private-equity firm. Plus, he noted, “If you wear a fancy watch, chances are someone else may be wearing the same one.” Tenenbaum runs little risk of twinning with a colleague when he straps on his Mickey Mouse or Snoopy Swatches, worn with premium Brioni or Zegna suits.
Evan Vladem, 37, considers his Casio calculator watch a neat “ice breaker” when schmoozing, a professional obligation for the partner at a financial advisory in Fort Lauderdale, Fla. “It came in handy to break up awkward moments,” he said of the black, $30-ish design, a Casio classic. At a dinner with an insurance partner a few years ago, he recalls, the conversation petered out after an exchange about a client’s situation, which involved some financial arithmetic. “I pulled out my wrist and said, with a smile, ‘Well, I’m happy I have my trusty calculator watch to help me here,’” said Vladem. “We both laughed. [It] kicked off another conversation.”
Even men who have invested heavily in high-end horology seem to be falling for cheap, kitschy designs. Scott Jay Kaplan, 44, a film producer and financier for Brooklyn company CoverStory, owns pricey models from Rolex and Audemars Piguet. But for daily wear he’s currently favouring a super-chunky $25 watch he bought in Argentina this past winter, a model similar to a G-Shock but by an unfamiliar brand. He says he has received a lot of compliments on it, and it has held up surprisingly well. “I bought it because it looked silly,” he said. “Not for clout.”
McDonough, the Charlie Brown fan, urges anyone considering a novelty ticker to follow just one rule: Don’t splurge. “I think the whole idea of luxury watch brands coming out with ‘kitsch’ watches is…a little bit absurd,” he said. “So anything over, say, $500 would be out.”
Prop styling by Marina Bevilacqua
The Wall Street Journal is not compensated by retailers listed in its articles as outlets for products. Listed retailers frequently are not the sole retail outlets.
This stylish family home combines a classic palette and finishes with a flexible floorplan
Just 55 minutes from Sydney, make this your creative getaway located in the majestic Hawkesbury region.
